They say that being in a band is like being married. Well, in the case of Lollapalooza and the City of Chicago, I would say the same goes for the relationship between a city and festival promoters, especially when they look in each other’s eyes and sign a 5-year, multi-million dollar deal to show how committed both sides are. And like a gradually growing relationship, where two partners begin to feel each other out, Lollapalooza and Chicago have grown more comfortable together with each passing year since the festival situated itself in Chicago’s Grant Park in 2005.

After the success in 2006, festival organizer Perry Ferrell and event promoters C3 Present’s promoters signed the 5-year deal with the City of Chicago, reserving the right to rock historic Grant Park for three days in August. And judging by the first ever sell-out crowd (75,000 per day), the relationship seems to be progressing nicely.

Though it was a much more crowded Lollapalooza this year, it was also by far the most solid bill with 120-plus artists from around the globe, including underground artists and established superstars, as well as some of Chicago’s independent bands mixed in to add some hometown cred. On the surface it was all about the music and the usual corporate sponsorship, but one stroll through the grounds made it clear that, with all eyes focused on Beijing, China this month for the Summer Olympics, Lolla also doubled as a showpiece for Chicago, a hopeful contender to host the 2016 games.

The backdrop of Chicago’s historically beautiful city setting also allows Lollapalooza to separate itself from other festival’s based on setting alone. And in a saturated summer music festival industry, where the similar bills don’t make a festival unique anymore, a setting like Chicago gives the promoters a valuable geographic and aesthetic benefit for fans.

By the end of the first day, Radiohead filled up Grant Park with sweet stretches of In Rainbows, as the euphoric croon of front man Thom Yorke allowed the band to pick up right where they left off when they filled Grant Park back in 2001 with the same symphonic wonder. Fans stood awestruck as fireworks blasted above while down below Radiohead merged melodic force with gentle whispers, covering a massive range of emotions. The band also made full use of their giant LED color screen towers that flashed a hypnotic kaleidoscope of reds, greens, and blues, punctuating each emotive lyrical turn.

The rest of the weekend felt like I was running through a large old school-style radio AM/FM tuner dial. As I journeyed back and forth across the grounds from the North and South main stages, tuning in to a few preset favorites—Gnarls Barkley, Brazilian Girls, Bloc Party, Battles—I also came across unexpected frequency pleasures at the middle-of-the-dial side-stages where a few bands tuned me in and took me for a ride.

It was sunny shoegazing in the park as Austin’s Explosions In The Sky tossed out an expansive picnic blanket for fans to chill out on that was threaded with thundering fuzzy noise rock and soft and subtle murmurs. Local DJ Bald Eagle kept the Saturday-afternoon-in-the-park vibe going by dropping banging beats of house and funk, and kept everyone moving by splicing in an appropriate sample of Chicago’s “Saturday in the Park”.
Chicago rapper Lupe Fiasco has come a long way from the backpack-rapper, skateboard labeling prior to his “Kick, Push” hit single from his debut Food & Liquor.

The Fiasco that took the stage here has fully transformed into a compelling performer that seamlessly blends hip-hop, soul, and rock. Decked out in a gleaming white vested suit and tie, Fiasco glided through several tracks from his latest effort, the stellar and ambitious concept album The Cool, while dropping two Food & Liquor hits, “Daydreamin’” and “Kick, Push” as well. With a polished soulful swagger and deftly orchestrating a full band behind him, Fiasco answered the call of his own song and proved that the time is here for him to be a “Superstar”.

On the other side of the career trail, though, nostalgia can certainly make fans want to rock, so hard in fact that the hedonism turns to mosh-pit masochism.

There’s no denying the influential rhythmic force of Rage Against the Machine, but it’s that same awesome feeling of being devoured by one of their songs that kept the show from being a nice controlled glimpse into the glory days of rap-rock’s early days.

Three separate times, front man Zach De La Rocha pleaded with the crowd to stop crushing each other at the front of the stage. It was a nasty sight as fans in the front row passed out and the music became secondary.

At the south end of the site Wilco, yet again, played a near flawless set, complete with slick, yet quirky, matching Spanish-Tex-Mex suits that made them look like extras in the last scene of Three Amigos. Nonetheless, with the city skyline twinkling behind them, the alt-rock quintet went about their business with a superb set that dipped into Yankee Hotel Foxtrot, Summer Teeth, and Sky Blue Sky, and I think a heard a new one in there as well.

In order to enjoy the festival, though, you have to take a break. And Lollapalooza offers one of the best chances to rest, educate, and entertain in the shade via a movie theatre (playing The Flaming Lips’ Christmas on Mars), and the environmentally focused Green Street’s row of booths.

But it was the entertaining jaunt through Kidzapalooza, a Lolla staple where kids (and their rock-focused-parents) could learn the chords and rhymes schemes of hip-hop via workshops and demonstrations that actually prepared me for what followed.

Poet/actor/emcee Saul Williams—with a swath of blue war paint across his face—dropped feathers upon the heads of those crammed into the narrow confines of the Citi stage. As he’s done before, Williams unleashed lyrical fire and volcanic rhythms, coupled with earth-quaking tempos.

Those new to Williams watched on the fringes in eye-popping curiosity as fans pumped their arms to the punk, hip-hop, funk hybrid, filling up the street and rocking the concrete via cuts from Williams’ Inevitable Rise and Liberation of Niggy Tardust. The set climaxed as Williams beckoned the crowd, “Do you realize that the power is in our heart and hands? Are you with me?” The crowd raised their fists and roared. “Ya’ll just don’t understand,” he responded. “That means everything!” It wasn’t his best show as he took a few creative risks with the set list, but it converted the curious as well as those politely waiting for the pop-splicing biochemist phenom Girl Talk who followed Williams’ set.

Like a human beat accordion, Greg Gillis (aka Girl Talk) went right into the lead track from this year’s Feed the Animals. Hungry fans jumped up on the stage.

The stage tech fired streams of toilet paper from shotgun shooters and the crowd space grew denser and denser as the beats got faster and faster, with Gilllis turning up the intensity and cranking out a set that mixed the Spencer Davis Group’s “Gimmie Some Lovin’”, with southern crunk and Soulja Boy.

Back on the AT&T stage Gnarls Barkley—the duo of crooner Cee-Lo and Brian Burton (aka Danger Mouse)—slowly pulled the curtain off a much-subdued yet soulful, slow-burning set. Much different from the massive surge they created in 2006 with the psycho-soul hit “Crazy”, the set was more lilting, disappointing fans who hoped for a booty shot of neo-Motown adrenaline.

With the hype of a possible appearance and introduction by Senator Obama, Kanye West’s set was dripping with anticipation. On top of that, West also faced the challenge of erasing the backlash of his delayed Bonnaroo set a few month ago. Several “Kanye Sucks”(front) / “Bonaroo ’08”(back) t-shirts were spotted Sunday afternoon and most haters went to see Trent Reznor as Nine Inch Nails played opposite of West Sunday night.

But while it’s easy to hate Kanye West, the things that provoke such ire are the same things that make him a star. He is a true performer and a gifted songwriter and producer, and his non-musical antics emanate from that same unashamed lyrical impulse to express whatever he is feeling in his heart. In turn, this transformed his set into a hometown shout-out spectacle that could’ve alienated (as we know was West is capable of) but did the complete opposite.

From the show stopping dedication to his late mom to the stripped-down version of the current stage prop-heavy Glow in the Dark tour, West put the weight of the show on his own shoulders. His own ability to freestyle elevated the show to a place beyond the temporal flashing lights of celebrity glitz.

He delivered the goods like an artist who has the right to boast and song for song, lyric to lyric, was digging for the center of each heart connected to each set of arms that were slicing the air on beat.

It’s validated boasting. Haters can’t deny it and fans want more of it. Most of all, it was startling to see how much West has grown as a performer from when I last saw him during the Late Registration tour, which was musically stunning but fell short because of his defensive performance and full-blown arrogant attitude and swagger.

But this show revealed a transformation. He somehow found a way to channel all the sadness, grief, and sorrow following the loss of his mother and combined that emotive power with the pride of playing in front of a hometown crowd (Grant Park is just a few miles from where he grew up).

Taking full advantage of those two emotional allies West put on a show that soaked the crowd in pure cathartic emotion.

West’s set was a fantastic end to a festival that was one of the few major summer festivals, so far, to actually increase ticket sales. If they have a bill of similar stature next year they’ll need to expand. Here’s my suggestion (if they’re not already in the works): Extend south and rent out Solider Field, go east and create a floating venue over Lake Michigan, and build a Lolla CTA-sponsored monorail to transport fans around the venue. I’m sure all those will work well with the Olympic foresight.